…and many other kinds of geekery by comicgeek, gadgetfreak and God's girl Katarina

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Ever since I bought my iMac back in 2011 (16 Gb RAM, core i7 processor), I had been working with Mac OSX 10.7 – otherwise known as Lion. I never upgraded, for I firmly believed in the adagium “if it ain’t broke, don’t fix it”.

However, this also meant that more and more applications had reached their maximum update level, among which Safari – which meant that slowly but surely more and more websites no longer fully functioned. Sites like Youtube and Twitter, to name but a few. So the level of my user annoyance gradually increased, until I reached the point of feeling ready to move on from Lion after all.

When Apple announced their latest MacOS “Sierra” to be expected this Fall, I suspected I would not be able to make the jump from Lion. So if ever I planned to upgrade after all, I had to do it now.

Since I had to jump four iterations of MacOS (from OSX 10.7 to OSX 10.11) in one fell swoop, I chose to take as little risk as possible and go with a clean install. After much reading and research I also chose to do this from a bootable flash drive/usb drive.

Since I had never undertaken such an adventure, and had to do lots of Googling and Trying of Things, I decided to write every step down for you all – but only the successful ones, so your path might be shorter and smoother. So here we go…

…but before you move on, please consider carefully that a clean install will erase everything, and I mean Every Thing, from your Mac’s hard drive. This not only includes your files and applications, but also your user accounts and network settings. Know that in most cases a so-called “over-the-top install” (in which you simply install the new OS over the previous one, without erasing everything) works perfectly fine. I chose a clean install because as I said I had a pretty large “jump” between OSes to make, which also stood for a time leap of about 5 years. Years in which a lot of “baggage” had accumulated, like unused extensions, app support files, preferences etc. These could potentially pose security risks or app instability in the new system, or simply take up too much space. A clean install would be like setting up my l’ill ol’ Mac as if it came brand new out of the box – at least on the inside 😉 .

Please also make sure that all of your mission critical apps are all compatible with El Capitan, before you do the install… The safest way to ensure this is probably to visit the developer’s website. You can also checkout RoaringApps.com, although I’m not certain how reliable they are in all instances.

Okay, if you still want a clean install after all this, please read on for my own step-by-step process.

1. Clean up
Throw away files and applications that you no longer use or haven’t used in a long time. Use an app like AppCleaner to make sure every little file associated with an application is thrown out as well.

If you want to rearrange things and/or throw out garbage, do so now, before you make a cloned copy (steps 1-4).

2. Close all applications, update them, log them
Make a note which apps came from the Mac App store and can be readily recovered, and which apps require you to download a new installer from the developer’s website.

Also, you may want to have a log of all of your application licenses in a copyable format so that you can paste it in when reinstalling your apps (after the install of El Capitan).

3. Log off from cloudapps like Dropbox, Evernote, etc. Do this last and don’t edit anymore cloud files until after the clean install.

4. Disconnect any unnecessary peripherals such as printers, tablets, microphones, etc. Try to work with just attached drives and a wired mouse and keyboard.

6. Repair boot drive permissions
Use Disk Utility to make sure your boot drive permissions are all repaired and that the disk directory is verified as good.

7. Back up
This may be the single most important action you should take. Back up, back up, backup! Use Time Machine, but if you really want to be safe, also make a complete cloned copy of your Mac. I used Carbon Copy Cloner for that, for it is able to make bootable backups. You can try it out for free, which is perfect for opportunities like this.

Note: you will need a second external harddrive for the cloned copy, do not try to cram it in next to your Time Machine backup, for Troubles might await you and you do not want to take risks with your backups…

8. Download El Capitan from the Mac AppStore
It will launch automatically but you need to quit (CMD-Q) out of the upgrade process.

9. Create a bootable installer flash drive
Click here for an explanation how to. Move the installer file from your Applications folder to your bootable flash drive. It’s about 6 gigabytes, so make sure your flash drive is at least 8 Gb, and doesn’t have any files on it.

10. Connect the bootable USB El Capitan install drive to the Mac and install El Capitan
Since this process has been described by many others, I’ll simply refer you to the one that I found most helpful and easiest to understand. Click here for those step by step instructions.

In my case this process took 40 minutes. Which I thought was pretty fast, but as stated above my Mac does have a Core i7 processor with 16 Gb RAM, so if you have a different setup it might take more – or even less – time than mine.

11. Restore your data
Right after you boot El Capitan the setup process will start. You can elect to restore user accounts and settings from Time Machine. I chose the following set of restore options: Users folder + Settings + Other files and folders: Yes; Applications: No.

By the way, when you sign into iCloud it will sync up anything you had previously selected in iCloud sync settings. This may include your mail (after you rebuild or log in to your account), calendar, contacts, reminders, Safari bookmarks, iCloud Keychain etc.

The same goes for your other cloud apps like Dropbox and Evernote (etc): as soon as you login to their desktop apps, your files will automatically reappear on your Mac.

12. Reinstall your apps
In step 2 you made a list of Mac App Store apps, and apps directly from a developer’s site. You can now use that list to restore your apps.

If you were using any cloud-based apps like Dropbox, Box, Evernote etc. you can simply download their desktop application installers, install the desktop apps, log in and you’re back in business.

In case anything goes wrong, or if it goes well but you’re not satisfied with the new system
Take the current Time Machine backup you made in step 7, you can boot from the recovery partition (CMD-R), do a complete erase (Disk Utility) and then restore from your Time Machine archive. You’ll be back where you were before you started.

Issues I encountered after the install

There were three major applications that no longer worked after I had installed El Capitan. Two of those I knew beforehand, but the biggest one took me by surprise and forced me to purchase a software update. They were:

Parallels Desktop 7 – this version is not compatible with El Capitan, an issue of which I was aware before I started. If I want to continue to use Parallels, I cannot upgrade (the more affordable option) for the jump from 7 to 11 is simply to big. I’ll have to buy a new, full version.

iMovie ’11 – it is still available in El Capitan but I could not get it to work the way I wanted it to, so I had to switch to the latest iMovie. Of this I was not particularly aware beforehand, I mean I did know there was a new iMovie but I had hopes the older version would still work satisfactorily. Which it didn’t and since a lot had changed between these versions, I actually had to sign up for an iMovie workshop in an Apple store to be able to work with it again. I still don’t really like the new version, but what can one do – I guess I’m going to have get over it.

Microsoft Office 2011. Now this one not working surprised me, and I don’t mean in a positive way. I could not get Word, Excel or Powerpoint to work at all, they wouldn’t even start. (I don’t use Outlook). Searching on the internet taught me that many struggled with this problem. There had been some fixes from Microsoft, mainly aimed at Outlook, but for the other three there were no fixes at hand as of yet. Since Office to me is mission critical, I experienced a light panic. I tried Pages for a couple of days, and even the open sourced LibreOffice, but both did not function the way I needed them to, for my specific wants & needs (I create written tutorials with lots of pictures, and inserting these pictures the way I wanted them to was a complete train wreck in both of those programms). After a week of trying (and cursing) I gave in, for I had to move on with my work. So I purchased Microsoft Office 2016 – which works like a dream with El Capitan I have to say, but confronted me with an unexpected expense.

In conclusion

These were the steps I took to go from Mac OSX 10.7 Lion to 10.11 El Capitan with a clean install. It took me many hours to research the many options and possibilities and finally I settled on the above set of steps. They are of course based on my personal choices and preferences, and given my particular hardware system setup. Nevertheless I feel quite confident that in most cases these steps will work, which is why I took the trouble of logging them here for you all, so as to spare you the same amount of hours of research (and doubts, and annoyances) I went through.

I hope this will be of help to at least some of you. I hope you feel encouraged by the fact that I, a simple user and not a software engineer nor any kind of other tech expert, have managed to sail through these steps successfully and have already enjoyed my new El Capitan OS for some weeks before I published this.

And when Sierra comes, I can now move confidently forward with a simple over-the-top install.